The Smallest Town You’ll Ever Get Lost In

Navigating around a town of about 25,000 should be pretty easy. Often I can do it without a map–after all, how hard can it be to find 1435 N. Fourth St.?

But they broke the mold when they made Kingston, NY, population 23,893. Located along the Hudson River in the shadow of the Catskill Mountains, the city results from the merger of three small villages, today known as Uptown, Midtown, and Downtown.

Uptown, originally named Esopus as it abuts Esopus Creek, is also known as the Stockade District. It’s the location of the Court House and the county government buildings. It’s where I go to get my driver’s license renewed. The main shopping street–also a tourist destination–is Wall Street.

Downtown is often called Rondout, named after Rondout Creek. More accurately a river, it is a major tributary of the Hudson and serves as the city’s harbor. Along the waterfront, beside the park, are numerous restaurants, taverns, and shops.

Rondout Creek waterfront (courtesy of City of Kingston)

Suspension bridge over Rondout Creek. (Wikipedia–Creative Commons)

Between Uptown and Downtown is Midtown–I don’t know the original name. It is the least photogenic of the three neighborhoods, with stores meant for local residents. My wife and I bought a new stove there.

So each of these three villages has its own street grid. The streets of Uptown run parallel and perpendicular to Esopus Creek. Likewise, Downtown’s roads are oriented to Rondout Creek. And Midtown’s main drag is called Broadway, with side streets organized accordingly.

These street patterns don’t fit together. Midtown’s Broadway, for example, should connect Uptown with Downtown. And I suppose it does, after a fashion. It misses Uptown by about half a mile–it’ll take some meandering to actually get to the courthouse.

It misses Downtown by the same distance, though a street with the same name makes a sharp right turn and will eventually get you there.

Modern traffic engineers have worked to make the town navigable. Route 9W is now a limited access highway that cuts straight through town. And Broadway ends at the entrance I-587, billed as the shortest interstate highway in the country–a bit over a mile long. It bypasses Uptown, allowing people to get to the NY Thruway without getting lost.

But the old state highways that go through Kingston are a different story–the one from my house is Route 32. From the southern city limit to the northern is about 3.7 miles. Below are the Google directions for the route. Whatever else you do, don’t try to drive in a straight line.

So here’s my challenge for your first trip to Kingston: There’s a Mexican restaurant located at 97 Abeel Street. See how long it takes you to find it. Using a GPS is cheating.

You’ll be mighty hungry by the time you get there. Let me know how you do.